Wavelength dependent photoextrusion and tandem photo-extrusion reactions of ninhydrin bis-acetals for the synthesis of 8-ring lactones, benzocyclobutenes and orthoanhydrides

Wei Sun; Surajit Kayal; William A.T. Raimbach; Xue Zhong Sun; Mark E. Light; Magnus W.D. Hanson-Heine; Michael W. George; David C. Harrowven

doi:10.1039/d1cc06800h

Wavelength dependent photoextrusion and tandem photo-extrusion reactions of ninhydrin bis-acetals for the synthesis of 8-ring lactones, benzocyclobutenes and orthoanhydrides

Wei Sun
, Surajit Kayal
, William A.T. Raimbach
, Xue Zhong Sun
, Mark E. Light
, Magnus W.D. Hanson-Heine
, Michael W. George
, David C. Harrowven

Department of Chemical and Environmental Engineering

Research output: Journal Publication › Article › peer-review

4 Citations (Scopus)

Abstract

Ninhydrin bis-acetals give access to 8-ring lactones, benzocyclo-butenes and spirocyclic orthoanhydrides through photoextrusion and tandem photoextrusion reactions. Syntheses of fimbricalyxlactone B, isoshihunine and numerous biologically-relevant heterocycles show the value of the methods, while TA-spectroscopy and TD-DFT studies provide mechanistic insights on their wavelength dependence.

Original language	English
Pages (from-to)	1546-1549
Number of pages	4
Journal	Chemical Communications
Volume	58
Issue number	10
DOIs	https://doi.org/10.1039/d1cc06800h
Publication status	Published - 4 Feb 2022

ASJC Scopus subject areas

Electronic, Optical and Magnetic Materials
Catalysis
Ceramics and Composites
General Chemistry
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

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10.1039/d1cc06800h

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Sun, W., Kayal, S., Raimbach, W. A. T., Sun, X. Z., Light, M. E., Hanson-Heine, M. W. D., George, M. W., & Harrowven, D. C. (2022). Wavelength dependent photoextrusion and tandem photo-extrusion reactions of ninhydrin bis-acetals for the synthesis of 8-ring lactones, benzocyclobutenes and orthoanhydrides. Chemical Communications, 58(10), 1546-1549. https://doi.org/10.1039/d1cc06800h

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title = "Wavelength dependent photoextrusion and tandem photo-extrusion reactions of ninhydrin bis-acetals for the synthesis of 8-ring lactones, benzocyclobutenes and orthoanhydrides",

abstract = "Ninhydrin bis-acetals give access to 8-ring lactones, benzocyclo-butenes and spirocyclic orthoanhydrides through photoextrusion and tandem photoextrusion reactions. Syntheses of fimbricalyxlactone B, isoshihunine and numerous biologically-relevant heterocycles show the value of the methods, while TA-spectroscopy and TD-DFT studies provide mechanistic insights on their wavelength dependence.",

author = "Wei Sun and Surajit Kayal and Raimbach, \{William A.T.\} and Sun, \{Xue Zhong\} and Light, \{Mark E.\} and Hanson-Heine, \{Magnus W.D.\} and George, \{Michael W.\} and Harrowven, \{David C.\}",

note = "Publisher Copyright: {\textcopyright} 2022 The Royal Society of Chemistry.",

year = "2022",

month = feb,

day = "4",

doi = "10.1039/d1cc06800h",

language = "English",

volume = "58",

pages = "1546--1549",

journal = "Chemical Communications",

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publisher = "Royal Society of Chemistry",

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Sun, W, Kayal, S, Raimbach, WAT, Sun, XZ, Light, ME, Hanson-Heine, MWD, George, MW & Harrowven, DC 2022, 'Wavelength dependent photoextrusion and tandem photo-extrusion reactions of ninhydrin bis-acetals for the synthesis of 8-ring lactones, benzocyclobutenes and orthoanhydrides', Chemical Communications, vol. 58, no. 10, pp. 1546-1549. https://doi.org/10.1039/d1cc06800h

TY - JOUR

T1 - Wavelength dependent photoextrusion and tandem photo-extrusion reactions of ninhydrin bis-acetals for the synthesis of 8-ring lactones, benzocyclobutenes and orthoanhydrides

AU - Sun, Wei

AU - Kayal, Surajit

AU - Raimbach, William A.T.

AU - Sun, Xue Zhong

AU - Light, Mark E.

AU - Hanson-Heine, Magnus W.D.

AU - George, Michael W.

AU - Harrowven, David C.

PY - 2022/2/4

Y1 - 2022/2/4

N2 - Ninhydrin bis-acetals give access to 8-ring lactones, benzocyclo-butenes and spirocyclic orthoanhydrides through photoextrusion and tandem photoextrusion reactions. Syntheses of fimbricalyxlactone B, isoshihunine and numerous biologically-relevant heterocycles show the value of the methods, while TA-spectroscopy and TD-DFT studies provide mechanistic insights on their wavelength dependence.

AB - Ninhydrin bis-acetals give access to 8-ring lactones, benzocyclo-butenes and spirocyclic orthoanhydrides through photoextrusion and tandem photoextrusion reactions. Syntheses of fimbricalyxlactone B, isoshihunine and numerous biologically-relevant heterocycles show the value of the methods, while TA-spectroscopy and TD-DFT studies provide mechanistic insights on their wavelength dependence.

UR - https://www.scopus.com/pages/publications/85123969048

U2 - 10.1039/d1cc06800h

DO - 10.1039/d1cc06800h

M3 - Article

C2 - 35014645

AN - SCOPUS:85123969048

SN - 1359-7345

VL - 58

SP - 1546

EP - 1549

JO - Chemical Communications

JF - Chemical Communications

IS - 10

ER -

Wavelength dependent photoextrusion and tandem photo-extrusion reactions of ninhydrin bis-acetals for the synthesis of 8-ring lactones, benzocyclobutenes and orthoanhydrides

Abstract

ASJC Scopus subject areas

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